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Method of forming a dry quaternary ammonium salt mixture

a technology of quaternary ammonium salt and mixture, which is applied in the preparation of isocyanic acid derivatives, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of affecting subsequent reactions, affecting the effect of subsequent reactions, and affecting the quality of the reaction vessel, so as to achieve the effect of accurately adding the solid material to the reaction vessel

Inactive Publication Date: 2010-08-10
SHPP GLOBAL TECH BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method effectively reduces water content in quaternary ammonium salts to less than 25 ppm, minimizing decomposition products and ensuring the salts are suitable for commercial-scale reactions with high yield and purity.

Problems solved by technology

Straightforward methods of drying the quaternary ammonium salt solid such as heating in an oven can result in the formation of significant amounts of degradation products, which can then interfere with or negatively influence subsequent reactions.
Additionally when the quaternary ammonium salt is used as a catalyst for commercial scale reactions it can be difficult to accurately add the solid material to the reaction vessel.

Method used

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  • Method of forming a dry quaternary ammonium salt mixture
  • Method of forming a dry quaternary ammonium salt mixture
  • Method of forming a dry quaternary ammonium salt mixture

Examples

Experimental program
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Effect test

example 1

[0042]A 1000 milliliter (mL), 3-necked, round-bottomed flask, was equipped with a magnetic stir bar, a reflux condenser, an external temperature controlled oil bath, a receiver topped with a reflux condenser, and a nitrogen gas sweep. The receiver was configured such that the bottom layer of ODCB that collected in the receiver was diverted back into the vessel with a three-way valve. The receiver was also modified to include an additional cooler.

[0043]The bulk water was removed as follows: The vessel was charged with 200 grams of aqueous HEGCl brine solution. The flask was then charged with 400 grams of ODCB. The solution was stirred magnetically. The temperature of the oil bath was slowly raised to 120° C. to 140° C. at which point the water / ODCB azeotrope began to distill overhead. The vapor condensed and formed two layers in the receiver. The ODCB phase that collected in the receiver was allowed to return to the vessel, and the water was drawn off to an external flask. Then the o...

example 2

[0048]The procedure in Example 1 was followed, using the same proportions specified in Example 1, except that the aqueous HEGCl brine solution was slowly added to ODCB that was already maintained at 120° C. to 180° C. The water / ODCB was taken overhead and the condensed ODCB phase returned to the vessel to maintain an optimal operating level and concentration of HEGCl in ODCB. Once the bulk water was removed, dry ODCB was added to the vessel and ODCB distilled overhead until the water in the pot was less than about 30 ppm. The sodium chloride was removed by the method described in example 1.

example 3

[0049]The procedure in Example 1 for removal of bulk water was followed. After the removal of the bulk water the sodium chloride (which had agglomerated) was filtered off to afford a wet ODCB / HEGCl solution that contained about 10,000 ppm to 1000 ppm water. The wet filtered ODCB / HEGCl solution was further dried by distillation of ODCB, while maintaining the concentration of the HEGCl solution at 15 weight % by the addition of dry ODCB while ODCB is being distilled off, to afford an ODCB / HEGCl solution containing less than about 30 ppm water.

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Abstract

Disclosed herein is a method comprising:(a) adding an aqueous solution comprising a quaternary ammonium salt to an organic solvent in a vessel under an inert atmosphere, thereby forming a first mixture comprising the quaternary ammonium salt and the solvent; and(b) mixing the first mixture at a temperature and for a time sufficient to remove water and a portion of the solvent from the first mixture,wherein the mixing is performed in an inert atmosphere and the temperature is less than the decomposition temperature of the quaternary ammonium salt.

Description

BACKGROUND OF INVENTION[0001]This disclosure is related to removing water from quaternary ammonium salts.[0002]Quaternary ammonium salts are used in a wide variety of reactions. Frequently quaternary ammonium salts are used as phase transfer catalysts. In some reactions the presence of water in the phase transfer catalyst decreases the amount of product produced by the reaction or, in some cases, prevents the reaction from occurring. While quaternary ammonium salts can be used in solid form, the solid form can contain water as many quaternary ammonium salts absorb water from the atmosphere. Straightforward methods of drying the quaternary ammonium salt solid such as heating in an oven can result in the formation of significant amounts of degradation products, which can then interfere with or negatively influence subsequent reactions. Additionally when the quaternary ammonium salt is used as a catalyst for commercial scale reactions it can be difficult to accurately add the solid mat...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C211/62C07D211/00C07C251/02C07D213/72
CPCC07C277/08C07D209/48C07D213/74C07C279/04
Inventor GUGGENHEIM, THOMAS LINKHOWSON, PAUL EDWARDKHOURI, FARID FOUADKLOPPENBURG, LIOBA MARIALITTLEJOHN, MATTHEW HALOBERHOLTZER, JACOB LEEORDONEZ, JUAN RODRIGUEZSRIRAM, SURESH R.WOODRUFF, DAVID WINFIELD
Owner SHPP GLOBAL TECH BV